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This is a major structural project you are talking about with replacing the roof with a different material, tying the buildings together, reinforcing ceiling joists. Party wall consent from both neighbouring properties which the freeholder would have to obtain. Soil may have a tendency to subsidence in the area. The disturbance to the freeholder whilst the building works occur. Unforeseen problems that occur once the project starts. I see red flags everywhere so witholding consent in this case is not unreasonable. Remember you do not own the property, you are on a long term lease.

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Probably should have expanded on the description of "subsidence" but it was merely the bay window to the front of the property, which was subsequently underpinned....

The structural surveyor was very complimentary of an extension (obviously as he'd be involved in its construction) but also as the roof and fabric of the building would be strengthened, tieing the party walls together and the heavy "red 22" tiles would be replaced by lighter slate.

If i was to ensure appropriate insurance, before, during and after the work, would this be deemed enough of a mitigator to the "risk"

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In this case I think the freeholder has a good case for not wanting a dormer and can withold consent. Adding additional weight to a property that has had subsidence may invalidate insurance for further subsidence. Problems could occur years down the line when you have sold and moved on.

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Consent - not to be unreasonably withheld.....

All

I own the first floor flat in a house.
My ownership is long leasehold (152yrs remaining)
The freeholder is the ground floor flat.

Many flats up and down the road have added an additional room/dormer window in the roof, so the precedent from a planning perspective is there.
The lease states that our demise includes the roof and roof space.

However

The lease states the following "not without the prior written consent of the lessor (which consent shall not be unreasonably withheld or delayed) to make or permit to be made any alterations or additions to the demised premises"

We have approached the freeholder to request her consent and she has said no, stating previous issues with subsidence (underpinned in 1994) as her rationale. But we have since had a structural surveyor round who has attested that the loading of a dormer extension is minimal and all the risk can be (over) engineered out.

Can anyone suggest whether there is an opportunity to push this forwards (through legal process or otherwise) or whether the "unreasonable" clause means we are stuck in a negotiating black hole??

Get some plans drawn up and stick them in is the only way to find out. There are too many variables for anyone unfamiliar with the site to give an opinion.
But if you come up with something sympathetic to the neighbourhood and the neighbours don't object then it could easily be waved through by...

Agree with all that ram said. There is no way i would allow that if I owned the flat below you. Because any problems with the roof and noise caused by you using your roof garden are going to be to the downstairs flat. Maybe you will get agreement who knows. But it really sounds a bad idea to me. Your...